Imidazole → HCID 57971146, compound

HRID 1890492Notes

Reaction equation

HRID 1890492 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2004934-Pyrimidinemethanol, 2-amino-

Product 1

HCID 57971146HCID 57971146, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-4-hydroxymethylpyrimidine (750 mg, 6.0 mmol, Reference Compound No. 4-1) and tert-butyldimethylsilyl chloride (990 mg, 6.6 mmol) were suspended in anhydrous N,N-dimethylformamide (8.0 mL), then imidazole (0.90 g, 13 mmol) was added thereto and the mixture was stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (50 mL), washed twice with saturated aqueous sodium hydrogencarbonate solution (50 mL), and then washed with brine (50 mL), and dried over anhydrous magnesium sulfate. Then the solvent was evaporated under reduced pressure, the precipitated solid was filtered off with 50% ethyl acetate-n-hexane solution, and dried under reduced pressure to give 1.2 g of the title Reference Compound as a white solid (Yield: 84%).

Workup

  1. washwashed twice with saturated aqueous sodium hydrogencarbonate solution (50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen the solvent was evaporated under reduced pressure
  5. filtrationthe precipitated solid was filtered off with 50% ethyl acetate-n-hexane solution
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d8a7d0c376af4a37aaaec25b942d2fd4
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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